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tioguanine

CHEBI:9555 EXACT SEEDED antiviralcytotoxicenzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.

Structure

Standard InChIKeyWYWHKKSPHMUBEB-UHFFFAOYSA-N
SMILESC1=NC2=C(N1)C(=S)N=C(N2)N
Stereochemistryfully defined
Cross-referencespubchem:2723601

Filing pathway

Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

TaxonBasisClusterEvidence
Erwinia amylovora CFBP1430
NCBITaxon:665029		 SOURCE_ASSERTION mibig:BGC0001992 PMID:29947149

Occurrences 2

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

TaxonSourceReference
Paris polyphylla var. chinensis
NCBITaxon:221254		 LOTUS DOI:10.1016/J.JPBA.2011.12.027
Pseudomonas
NCBITaxon:286		 LOTUS DOI:10.7164/ANTIBIOTICS.24.328

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0001992 Erwinia amylovora CFBP1430
NCBITaxon:665029 		CLUSTER_UNSTATED genbank:NC_013971.1

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 2 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT tioguanine CHEBI:9555 Alkaloids TARGETS & BIOACTIVITY 0 molecular targets 25 bioactivities · 0 graphs

Bioactivities 25

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

AssayResultTarget enzymeSource detail
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 16 hourOTHER 15.089 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1224888
assay
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 16 hour
evidence
  • reference
    pubchem.aid:1224888
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1224888, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
15.089
units
uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell PathologyOTHER 15.8489 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1645839
assay
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology
evidence
  • reference
    pubchem.aid:1645839
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
15.8489
units
uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell PathologyOTHER 15.8489 uM; NOT_DETERMINEDUniProtKB:O14656
pubchem.aid:1645839
assay
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology
evidence
  • reference
    pubchem.aid:1645839
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
15.8489
units
uM
target enzyme
UniProtKB:O14656
A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screenEC50 0.32 uM; ACTIVENot recorded
pubchem.aid:2252
assay
A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screen
evidence
  • reference
    pubchem.aid:2252
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2252, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory.
call
ACTIVE
measurement type
EC50
value
0.32
units
uM
activity class
CYTOTOXIC
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.OTHER 1.2995 uM; NOT_DETERMINEDNot recorded
pubchem.aid:624296
assay
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.
evidence
  • reference
    pubchem.aid:624296
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624296, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_056979 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
1.2995
units
uM
A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreenIC50 6.297 uM; ACTIVENot recorded
pubchem.aid:1985
assay
A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen
evidence
  • reference
    pubchem.aid:1985
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1985, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory.
call
ACTIVE
measurement type
IC50
value
6.297
units
uM
activity class
ENZYME_INHIBITOR
Acetylcholinesterase (AChE) small molecule antagonists: colormetric cell-based qHTS assayOTHER 21.8794 uM; ACTIVENot recorded
pubchem.aid:1347395
assay
Acetylcholinesterase (AChE) small molecule antagonists: colormetric cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1347395
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347395, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAA68151 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
ACTIVE
measurement type
OTHER
value
21.8794
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell lineOTHER 0.8327 uM; ACTIVENot recorded
pubchem.aid:2202236
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line
evidence
  • reference
    pubchem.aid:2202236
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202236, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.8327
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell lineOTHER 3.7197 uM; ACTIVENot recorded
pubchem.aid:2202237
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line
evidence
  • reference
    pubchem.aid:2202237
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202237, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.7197
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell lineOTHER 3.3152 uM; ACTIVENot recorded
pubchem.aid:2202234
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line
evidence
  • reference
    pubchem.aid:2202234
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202234, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.3152
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell lineOTHER 0.2955 uM; ACTIVENot recorded
pubchem.aid:2202233
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line
evidence
  • reference
    pubchem.aid:2202233
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202233, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.2955
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell lineOTHER 0.4174 uM; ACTIVENot recorded
pubchem.aid:2202232
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line
evidence
  • reference
    pubchem.aid:2202232
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202232, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.4174
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell lineOTHER 0.7422 uM; ACTIVENot recorded
pubchem.aid:2202231
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line
evidence
  • reference
    pubchem.aid:2202231
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202231, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.7422
units
uM
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell lineOTHER 2.9547 uM; ACTIVENot recorded
pubchem.aid:2202235
assay
BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line
evidence
  • reference
    pubchem.aid:2202235
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202235, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.9547
units
uM
Biochemical firefly luciferase enzyme assay for NPCOTHER 40.5334 uM; NOT_DETERMINEDNot recorded
pubchem.aid:624030
assay
Biochemical firefly luciferase enzyme assay for NPC
evidence
  • reference
    pubchem.aid:624030
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624030, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAA29795 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
40.5334
units
uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 5.31 uM; ACTIVENot recorded
pubchem.aid:1346979
assay
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346979
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346979, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
5.31
units
uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 9.6885 uM; ACTIVENot recorded
pubchem.aid:1346979
assay
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346979
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346979, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
9.6885
units
uM
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screenOTHER 3.7578 uM; ACTIVENot recorded
pubchem.aid:1346979
assay
Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346979
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346979, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.7578
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 5.958 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1346981
assay
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346981
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
5.958
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 8.6349 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1346981
assay
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346981
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
8.6349
units
uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screenOTHER 13.3332 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1346981
assay
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen
evidence
  • reference
    pubchem.aid:1346981
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
13.3332
units
uM
Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295ROTHER 0.7308 uM; ACTIVENot recorded
pubchem.aid:1963990
assay
Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R
evidence
  • reference
    pubchem.aid:1963990
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963990, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.7308
units
uM
activity class
CYTOTOXIC
Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295ROTHER 1.122 uM; ACTIVENot recorded
pubchem.aid:1963990
assay
Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R
evidence
  • reference
    pubchem.aid:1963990
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963990, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
1.122
units
uM
activity class
CYTOTOXIC
Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13OTHER 3.2643 uM; ACTIVENot recorded
pubchem.aid:1963989
assay
Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13
evidence
  • reference
    pubchem.aid:1963989
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963989, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
3.2643
units
uM
activity class
CYTOTOXIC
Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13OTHER 2.8184 uM; ACTIVENot recorded
pubchem.aid:1963989
assay
Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13
evidence
  • reference
    pubchem.aid:1963989
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963989, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.8184
units
uM
activity class
CYTOTOXIC
notes
775 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (tioguanine) ↗ MediaIngredientMech (CHEBI:9555) ↗ TaxonMech: Erwinia amylovora CFBP1430 (NCBITaxon:665029) ↗ PathwayMech (mibig:BGC0001992) ↗

Open questions 1

name-disagreement — ChEBI calls this structure 'tioguanine' and MIBiG calls it 'thioguanine'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.

Provenance

Source conceptSourceVersion
BGC0001992MIBIG3
CHEBI:9555CHEBI3-star

This page is generated from data/natural_products/alkaloids/tioguanine.yaml, which is generated from the committed inventories. Neither is edited by hand.